Vacation rentals with outdoor seating in Sugarloaf Key

We had a wonderful family vacation at Naomi’s place. The place was perfect for our family of 4. There was so much to do to keep our active family busy. The house was well stocked with everything you may need for meals. Host was very responsive and helpful throughout our stay. We rented a boat and the dock was perfect for storing. We are looking forward to staying here again on our next visit to the keys!

We loved our stay! The house was super clean and the back patio was beautiful. We loved the back canal area and saw lots of very cool wildlife and enjoyed fishing right there. Having the kayaks to use was also great. Beds were very comfy and the rooms were spacious. The house had everything we needed. We loved the key colony area. The cabana club was a great space and the house is in walking distance to Sunset Beach, which was beautiful. The whole area is super close to fun things to do and great restaurants. We would absolutely stay here again!

Great place to stay. It’s a house in a community with a lot of activities available. There’s an extra $125 fee for that, but it’s worth it.

This is a fantastic property! Right across from Sombrero Beach but still peaceful and private. The house and yard is like an oasis. Host and management company are WONDERFUL! Highly recommend!

Alfonso is a very responsive host who provided clear details, local recommendations (multiple of which we used), and provided a place in a great location. Neighbors are friendly. Place was clean. Perfect for our family with a 14 and 6 year old.

Thank you for sharing your beautiful home. We appreciate your wonderful suggestions and thoroughly enjoyed our dinner at El Siboney restaurant. Unfortunately the rain kept us from using the pool but we still had a fantastic time.

fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!

Great attached townhome/duplex with privacy fence between the other side. Great private pool just on the canal! The bottom story was perfect for extended family to have privacy but still be close! We even saw a manatee in the canal.

The condo and the whole condo complex was beautiful. The pool was great, with an awesome view. Plenty of places to sit at the pool and in the surrounding areas. One thing to note is that the condo has no closets and no place to hang clothes. Wasn’t a huge deal for us, as we were able to put things on shelves. Frank was very responsive when we needed something. The Marathon area has plenty of things to do and it’s close enough for a day trip to Key West.

Had a great stay here. Very nice and great location in the keys.

Wonderful, responsive host and a cozy place to stay with lots of character that’s super close to the action but far enough that you can’t hear the noise from the bars! Two blocks from Duval St, a couple minutes walk to other key attractions such as Blue Heaven, The Hemingway House and the Southernmost Point buoy and about a 15 minute walk to Fort Zachary Taylor Beach! The pool area is peaceful, cozy and a lovely place to chill!

Excellent location, very walkable to everything we wanted to do and see! Clean, well kept, and cute. Would visit again!

Exactly as listed. Megan was very helpful and responsive. You are right in Duval street. If you are coming for a few days, this is the place to stay at.

Reached out later on in the day for a sporadic trip to key west, immediate response from thomas with clear instructions. Quaint room in the best location, lots to do within walking distance. Really enjoyed our stay, we recommend it!

I had to call Mike because a breaker tripped and we could not find the breaker box. He responded immediately and directed us to the correct location. He also took the time to ask if we were enjoying the condo and if there was anything we needed.

We were on a girls trip and this was just enough room for four of us! Not a ton of amenities included, which host was clear about. Location is away from the hustle and bustle and we had lots of key deer come by! Bahia Honda was fabulous and a short drive away.

Great location and accommodations, friendly and prompt communications.

Fantastic Last-Minute Stay! We decided last minute—just the night before—to extend our stay in the Keys, as our kids were having a blast during their break. Our original place of stay in Marathon wasn’t available for another night, but thankfully, Frank’s place was. Even with our 11 p.m. booking, Frank was incredibly accommodating. He welcomed us warmly and communicated everything clearly, making check-in a breeze. If we take another family trip to the Keys, Frank’s place will be my first choice—I only wish we had found it sooner! The views of the water were stunning, and watching the sunset from the porch was truly exhilarating. Highly recommend!

Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.

Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

Everything was perfect for our stay at Airbnb, the pool felt amazing, the views were stunning, and the Uber drivers were incredibly fast. Even the locals agree that this is the best place to stay in Key West, and I couldn't agree more - I'll definitely be back. Our host, Traci, was absolutely top-notch!

This location is great! Duval Street was only 2 blocks away. Was able to walk to Cuban Queen coffee in the morning. Condo was everything that was described. Gated community with a pool. Couldn’t have asked for any more. Loni was a great communicator. Made sure we were able to find and get into condo. Proactive with communication.

Great Place! Everything was so easy from booking to checking out. Jennifer is very communicative, gives clear instructions and responds in a timely manner. The home is clean, comfy, has a very nice view, and we enjoyed sitting on the balcony and listening to the music from the restaurant down below (don't worry, the music stops at a reasonable hour). The downtown area is close enough for us to ride bikes. Publix grocery store is close by too. If we're ever back in Key West, we wouldn't hesitate to stay here again.

Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!